Pharmaceutical phenylacetonitrile derivatives

ABSTRACT

The present invention provides phenylacetonitrile derivatives of the general formula: ##STR1## wherein R 1 , R 2 , R 3 , R 4  and R 5 , which can be the same or different, are hydrogen or haolgen atoms or alkyl, alkoxy, nitro, amino or acylamino radicals and two adjacent substituents can together also form a methylenedioxy or ethylenedioxy radical, A is a radical of the general formula: ##STR2## in which R 6  is a straight-chained, cyclic or branched, saturated or unsaturated alkyl radical containing 2 to 12 carbon atoms, R 7  is a hydrogen atom or a straight-chained or branched, saturated alkyl radical containing up to 6 carbon atoms, m and n, which can be the same or different, are 2 or 3, p is 1 or 2 and X is a straight-chained, cyclic or branched alkyl radical containing 2 to 10 carbon atoms which is optionally substituted by an amino group or is a grouping of the general formula: ##STR3## wherein Y and Z, which can be the same or different, are straight-chained or branched alkyl radicals containing up to 8 carbon atoms or cycloalkyl, alkylcycloalkyl or cycloalkylalkyl radicals, in which these radicals are optionally interrupted by an oxygen or sulphur atom, and one of the groups Z in general formula II can also be a hydrogen atom or both Z groups are joined to form a ring containing 4 to 6 carbon atoms which is optionally interrupted by a further nitrogen atom which can be substituted by alkyl or alkanoyl, the --O--NO 2  groups being substituents of Y as well as of Z; as well as the salts thereof with physiologically acceptable acids. 
     The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.

The present invention is concerned with new phenylacetonitrilederivatives, with processes for the preparation thereof and withpharmaceutical compositions containing them.

Thus, according to the present invention, there are provided newphenylacetonitrile derivatives of the general formula: ##STR4## whereinR₁, R₂, R₃, R₄ and R₅, which can be the same or different, are hydrogenor halogen atoms or alkyl, alkoxy, nitro, amino or acylamino radicalsand two adjacent substituents can together also form a methylenedioxy orethylenedioxy radical, A is a radical of the general formula: ##STR5##in which R₆ is a straight-chained, cyclic or branched, saturated orunsaturated alkyl radical containing 2 to 12 carbon atoms, R₇ is ahydrogen atom or a straight-chained or branched, saturated alkyl radicalcontaining up to 6 carbon atoms, m and n, which can be the same ordifferent, are 2 or 3, p is 1 or 2 and X is a straight-chained, cyclicor branched alkyl radical containing 2 to 10 carbon atoms which isoptionally substituted by an amino group or is a grouping of the generalformula: ##STR6## wherein Y and Z, which can be the same or differentare straight-chained or branched alkyl radicals containing up to 8carbon atoms or are cycloalkyl, alkylcycloalkyl or cycloalkylalkylradicals, in which these radicals are optionally interrupted by anoxygen or sulphur atom, and one of the groups Z in general formula IIcan also be a hydrogen atom or both Z groups are joined to form a ringcontaining 4 to 6 carbon atoms which is optionally interrupted by afurther nitrogen atom which can be substituted by alkyl or alkanoyl, the--O--NO₂ groups being substituents of Y as well as of Z; as well as thesalts thereof with physiologically acceptable acids.

The physiologically acceptable acids can be, for example, hydrochloricacid, hydrobromic acid, sulphuric acid, phosphoric acid, acetic acid,malonic acid, succinic acid, fumaric acid, maleic acid, citric acid,tartaric acid, lactic acid, amidosulphonic acid, benzoic acid, oxalicacid, adipic acid, salicylic acid, naphthoic acid or o-acetoxybenzoicacid.

The new compounds according to the present invention contain at leastone asymmetric carbon atom. Therefore, the present invention alsoprovides all possible diastereomeric mixtures, racemates and alloptically-active forms of the compounds of general formula I.

A number of similar compounds are already known from Federal Republic ofGermany Patent Specification No. 11 54 810. However, the compounds ofgeneral formula I according to the present invention differ from thethere-described compounds in that they contain the grouping--O--X--(ONO₂)_(p) in at least one of the phenyl nuclei.

In comparison with the compounds described in Federal Republic ofGermany Patent Specification No. 11 54 810, the compounds of generalformula I according to the present invention possess superiorpharmacological properties.

Investigations on awake dogs with compounds according to FederalRepublic of Germany Patent Specification No. 11 54 810, such asverapamil, show a dosage-dependent decrease of the arterial bloodpressure and a dosage-dependent increase of the right atrial pressure,i.e. an after-load decrease but an increase of the pre-load. Incontradistinction thereto, the new compounds of general formula Iaccording to the present invention display a dosage-dependent reductionof the arterial blood pressure and also of the atrial pressure and thusof the pre-load. This is to be regarded as being an importanttherapeutic advantage since a lowering of the pre-load is a recognisedeffective therapeutic principle in the case of various diseases of theheart-circulatory system, for example in the case of angina pectoris andof cardiac failure.

Furthermore, in vitro investigations on blood vessels show that thecompounds of general formula (I), in contradistinction to those ofFederal Republic of Germany Patent Specification No. 11 54 810, increasethe content of cyclic guanosine monophosphate (c-GMP). According to theviews at present held, an increase of the c-GMP content results in ablood vessel relaxation which is an important therapeutic principle inthe case of heart-circulatory diseases.

The compounds of general formula I according to the present inventioncan be prepared, for example, by one of the following methods:

(a) subjecting a compound of the general formula: ##STR7## in which R₁,R₂, R₃, R₄, R₅, A, X and p have the same meanings as above and R₉ is ahydrogen atom or a group which can easily be split off, to a nitrateester formation reaction; or

(b) subjecting a compound of the general formula: ##STR8## in which R₁,R₂, R₃, R₄, R₅, A and Y have the same meanings as above and R₈ is ahydrogen atom or a lower alkyl radical, to an amide formation reactionwith a compound of the general formula:

    H.sub.2 N--Z--(ONO.sub.2).sub.p                            (V)

in which Z and p have the same meanings as above; or

(c) subjecting a compound of the general formula: ##STR9## in which R₁,R₂, R₃, R₄, R₅, A and Z have the same meanings as above, to an amideformation reaction with a compound of the general formula: ##STR10## inwhich R₈, Y and p have the same meanings as above; whereafter, ifdesired, the compound obtained is either reacted with an acid to give acorresponding salt or is reacted with a base to liberate a free basetherefrom.

Compounds of general formula III are obtained by reacting a compound ofgeneral formula IV with a compound of the general formula:

    H.sub.2 N--Z--(OR.sub.9).sub.p                             (V')

in which Z and p have the same meanings as above and R₉ is a hydrogenatom or a protective group which can easily be split off; or by reactinga compound of general formula VI with a compound of the general formula:##STR11## in which R₈, R₉, Y and p have the same meanings as above.

The nitrate ester formation reaction of compounds of general formulaIII, in which R₉ is a hydrogen atom or a protective group which caneasily be split off, can be carried out by reaction with a nitrateester-forming reagent, such as fuming nitric acid and acetic anhydrideor a mixture of fuming nitric acid and concentrated sulphuric acid, at alow temperature in the presence or absence of an inert solvent. Thereaction temperature is from ambient temperature to -60° C. andpreferably from -10° to -30° C. The mole ratio is from 1 to 10.

As protective group R₉, there are preferably used ester groups which,under the acidic conditions of the nitration reaction, are easily splitoff or exchanged for the nitrate group. Preferred protective groupsinclude the benzoyloxy, alkoxycarbonyl, alkanoyl and sulphonyl groups.Groups which are split off under basic conditions must possibly beremoved in a preceding reaction.

Alternatively, the nitrate ester formation reaction can also be carriedout in that, in a compound of general formula III, wherein R₉ is ahydrogen atom or an active ester or a sulphonyl group, the group OR₉ ishalogenated and the reaction product is subsequently reacted with silvernitrate in the presence or absence of a solvent at a temperature of fromambient temperature to 100° C.

The halogenation reaction can be carried out by processes known from theliterature by reacting a compound of general formula III with mesylchloride or tosyl chloride in the presence of an acid-binding agent andsubsequently the reaction product is reacted with an alkali metal halidein an organic solvent, for example dimethylformamide. The mole ratio ofthe mixture reaction between the halogen compound and silver nitrate isnot critical. It can be from 1 to 10. This reaction is also usuallycarried out at a temperature of from 20° to 100° C.

The amide formation reaction of a compound of general formula IV with acompound of general formula V can be carried out by reacting the twocompounds in an inert solvent, for example tetrahydrofuran, dioxan,dimethylformamide or methylene chloride, when R₈ in general formula IVis a lower alkyl radical. The reaction can be carried out at atemperature of from ambient temperature to 100° C., the reaction periodcan be from 1 to 10 hours and the mole ratio of the reactants can befrom 1 to 3.

When R₈ in general formula IV is a hydrogen atom, the amide formationreaction with a compound of general formula V can be carried out withthe help of a coupling reagent, for example dicyclohexylcarbodiimide orcarbonyldiimidazole, or by converting the carboxyl group in a compoundof general formula IV into an activated carboxylic acid derivative, forexample a carboxylic acid halide or mixed anhydride, by means of knownprocesses. As solvents, there can be used inert organic solvents, forexample, tetrahydrofuran, dioxan, dimethylformamide or methyl chloride.The reaction temperature is from -30° to +50° C., the reaction time isfrom 30 minutes to 10 hours and the mole ratio of the reactants can befrom 1 to 5.

The amide formation reaction of a compound of general formula IV with acompound of general formula V' can be carried out by reacting the twocompounds directly or in an inert solvent, for example tetrahydrofuran,dioxan, dimethylformamide or methylene chloride, for the case in whichR₈ in general formula IV is a lower alkyl radical and R₉ in generalformula V' is a hydrogen atom or a protective group. The reaction can becarried out between ambient temperature and 100° C., the reaction timecan be from 1 to 10 hours and the mole ratio of the reactants can befrom 1 to 3.

When R₈ in general formula IV is a hydrogen atom, the amide formationreaction can be carried out with a compound of general formula V' withthe help of a coupling reagent, for example dicyclohexylcarbodiimide orcarbonyldiimidazole, or by conversion of the carboxyl group in acompound of general formula IV into an activated carboxylic acidderivative, for example a carboxylic acid halide or mixed anhydride, forexample a halogenoformic acid ester, by means of known methods. Assolvents, there can be used inert organic solvents, for exampletetrahydrofuran, dioxan, dimethylformamide or methylene chloride. Thereaction temperature is from -30° to +50° C., the reaction time is from30 minutes to 10 hours and the mole ratio of the reactants can be from 1to 5.

The amide formation reaction of a compound of general formula VII orVII' with a compound of general formula VI can, in principle, be carriedout by the same processes such as are carried out in the case of thedescribed amide formation reactions from a compound of general formulaIV with a compound of the general formula V or V'.

The compounds of general formulae III, IV and VI can be prepared byreacting a compound of the general formula: ##STR12## in which R₁, R₂,R₃, R₄, R₅ and A have the same meanings as above, by known processeswith a compound of the general formula:

    Hal--X'--W                                                 (IX)

in which Hal is a halogen atom, such as chlorine or bromine, X' is astraight-chained or branched alkyl radical containing up to 8 carbonatoms, which is optionally substituted by an amino group, and W is ahydroxyl, amino, carboxyl or carbalkoxy group or a grouping which cansubsequently be converted thereinto or a carbon atom from X' and W cantogether form an epoxide ring.

The compounds of general formula VIII can be prepared, for example, byreacting a compound of the general formula: ##STR13## in which R₁, R₂,R₆, Hal and m have the same meanings as above and R₁₀ is a benzylradical, with a compound of the general formula: ##STR14## in which R₃,R₄, R₅, R₇ and n have the same meanings as above, according to knownprocesses, whereafter the benzyl radical is split offhydrogenolytically.

The compounds of general formula VIII can also be prepared by reacting acompound of the general formula: ##STR15## in which R₁, R₂, R₆ and R₁₀have the same meanings as above, with a compound of the general formula:##STR16## in which R₃, R₄, R₅, R₇, Hal, m and n have the same meaningsas above, whereafter the benzyl radical is split off hydrogenolytically.

The compounds of general formula III, IV, VI and VIII are new and someof them are also pharmacologically active.

The preparation of the compound of general formula X takes placeanalogously to known processes, for example by reaction of a compound ofgeneral formula XII with a compound of the general formula:

    Hal(CH.sub.2).sub.m Hal                                    (XIV)

wherein m has the same meaning as above and Hal is a chlorine or bromineatom, with the help of a phase transfer-catalysed reaction. The catalystused can be, for example, a quaternary ammonium or phosphonium salt or acrown ether.

The preparation of compounds of general formula XII also takes placeanalogously to known processes, for example by reaction of a compound ofthe general formula: ##STR17## wherein R₁, R₂ and R₁₀ have the samemeanings as above, with a compound of the general formula:

    R.sub.6 --Hal                                              (XVI)

wherein R₆ and Hal have the same meanings as above, with the help of aphase transfer-catalysed reaction. As catalyst, there can be used aquaternary ammonium or phosphonium salt or a crown ether.

Halogen means, according to the present invention, fluorine, chlorine,bromine and iodine, fluorine and chlorine being preferred.

Alkyl, also in alkoxy, means, insofar as it is not otherwise defined, aradical containing up to 6 carbon atoms, the methyl, ethyl, n-propyl,isopropyl and butyl radicals being preferred.

By cyclic alkyl radicals are to be understood mono- and dicycles,especially cyclopropyl, cyclopentyl and cyclohexyl radicals.

Especially preferred are compounds in which A in general formula I isthe radical: ##STR18##

By acylamino radicals are to be understood alkanoylamino radicalscontaining up to 6 carbon atoms, formyl and acetylamino being especiallypreferred.

The new compounds of general formula I according to the presentinvention and the salts thereof can be administered enterally andparenterally in liquid or solid form. As injection medium, it ispreferred to use water which contains the conventional additives forinjection solutions, such as stabilisers, solubilisers and buffers.Additives of this kind include, for example, tartrate and citratebuffers, ethanol, complex formers (such as ethylenediamine-tetraaceticacid and the non-toxic salts thereof) and high molecular weight polymers(such as liquid polyethylene oxide) for viscosity regulation. Solidcarrier materials include, for example, starch, lactose, mannitol,methyl cellulose, talc, highly dispersed silicic acids, high molecularweight fatty acids (such as stearic acid), gelatine, agar-agar, calciumphosphate, magnesium stearate, animal and vegetable fats and solid highmolecular weight polymers (such as polyethylene glycols). Compositionssuitable for oral administration can, if desired, contain flavouring andsweetening materials.

The compounds according to the present invention are usuallyadministered in amounts of from 50 to 500 mg. per day, referred to abody weight of 75 kg. It is preferred to administer, 2 to 3 times a day,1 to 2 tablets with an active material content of 20 to 200 mg. Thetablets can also be retarded in which case only 1 to 2 tabletscontaining 50 to 500 mg. of active material are given once per day. Theactive material can also be administered by injection 1 to 8 times a dayor by continuous infusion, amounts of from 10 to 200 mg./day therebyusually being sufficient.

Preferred compounds according to the present invention include thefollowing:

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

2-chloro-3-ethyl-4-{1-cyano-1-(methylethyl)-3-[N-methyl-N-[2-(3,4-dimethylphenyl)-ethyl]-aminopropyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

2-methoxy-5-{1-cyano-1-(cyclohexyl)-4-[N-ethyl-N-[2-(3,4-methylenedioxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

2-propoxy-4-{2-N-[4-cyano-4-(methylethyl)-4-(4-fluorophenyl)-butyl]-aminoethyl}-phenoxy-(2-nitrooxyethyl-1)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3-nitro-4-methoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxtpropyl-1)-acetamide

2-methoxy-4-{2-(N-methyl-N-[4-cyano-4-(methylethyl)-4-(3-amino-4-methoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3-acetamide-4-methoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl-1)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-methyl-3-nitrooxypropyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-5-{2-[N-methyl-M-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-aceticacid 4-(nitrooxymethyl)-piperidylamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid-4-(nitrooxymethyl)-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

3-{3-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl]-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[M-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

3-{2-[N-methyl-N-[4-cyano-4-hexyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

3-{2-[N-methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2-)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

4-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4-methyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(4,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4-dimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,4,4-trimethyl-3-nitrooxypentyl-2)-acetamide

3-{1-cyano-1-hexyl-4-[N-methyl-N-[2-(4-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamide

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-(2-nitrooxyethoxy)-phenylacetonitrile

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-(2-nitrooxypropoxy)-phenylacetonitrile.

α-isopropyl-α[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-(3-amino-2-nitrooxypropoxy)-phenylacetonitrile

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-(3-dimethylamino-2-nitrooxypropoxy)-phenylacetonitrile

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-(2-nitrooxyethoxy)-4-methoxyphenylacetonitrile.

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-(2-nitrooxypropoxy)-4-methoxyphenylacetonitrile

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-(3-amino-2-nitrooxypropoxy)-4-methoxyphenylacetonitrile

α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-(3-dimethylamino-2-nitrooxypropoxy)-4-methoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-(2-nitrooxyethoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-(2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-(3-amino-2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-(3-dimethylamino-2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(4-methoxy-3-(2-nitrooxyethoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(4-methoxy-3-(2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-isopropyl-α-{[N-methyl-N-[2-(4-methoxy-3-(3-amino-2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

α-ispropyl-α-{[N-methyl-N-[2-(4-methoxy-3-(3-dimethylamino-2-nitrooxypropoxy)-phenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

2-(nitrooxy)-N-{2-methoxy-4-}1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyethyl-2}-propionacidamide

4-(nitrooxy)-N-{2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-ethyl-2}-butyricacid amide

3-(nitrooxy)-2,2-dimethyl-N-{2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyethyl-2}-butyricacid amide

2-(nitrooxy)-N-{2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyethyl-2}-cyclohexanecarboxylic acid amide

4-(nitrooxy)-N-{2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyethyl-2}-cyclohexanecarboxylic acid amide

2-(nitrooxy)-N-{2-methoxy-4-{2-{N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl}}-phenoxyethyl-2}-propionicacid amide

4-(nitrooxy)-N-{2-methoxy-4-{2-{N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl}}-phenoxyethyl-2}-butyricacid amide

3-(nitrooxy)-2,2-dimethyl-N-{2-methoxy-4-{2-{N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl}}-phenoxyethyl-2}-butyricacid amide

2-(nitrooxy)-N-{2-methoxy-4-{2-{N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl}}-phenoxyethyl-2}-cyclohexanecarboxylic acid amide

4-(nitrooxy)-N-{2-methoxy-4-{2-{N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl}}-phenoxyethyl-2}-cyclohexanecarboxylic acid amide.

Also prepared are analogous compounds which, instead of the nitrooxygroup, have a hydroxyl group, as starting materials, as well as possiblyas pharmacologically active compounds.

In the following Tables, there are set out further compounds which areuseful according to the present invention:

    __________________________________________________________________________     ##STR19##                                                                    NZ,Z             R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR20##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR21##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR22##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR23##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR24##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR25##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR26##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR27##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR28##       OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                          OCH.sub.3                                    ##STR29##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR30##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR31##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR32##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR33##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR34##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR35##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR36##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR37##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR38##                                                                    NZ,Z             R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR39##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR40##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR41##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR42##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR43##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR44##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR45##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR46##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR47##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR48##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR49##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR50##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR51##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR52##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR53##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR54##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub. 3                                                                         OCH.sub.3                                    ##STR55##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR56##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR57##                                                                    NZ,Z             R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR58##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR59##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR60##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR61##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR62##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR63##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR64##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR65##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR66##       OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                          OCH.sub.3                                    ##STR67##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR68##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR69##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR70##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR71##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR72##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR73##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR74##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR75##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR76##                                                                    NZ,Z             R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR77##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR78##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR79##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR80##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR81##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR82##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR83##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR84##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR85##       OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                          OCH.sub.3                                    ##STR86##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR87##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR88##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR89##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR90##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR91##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR92##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR93##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR94##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR95##                                                                    NZ,Z           R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                       __________________________________________________________________________     ##STR96##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR97##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR98##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR99##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR100##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR101##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR102##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR103##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR104##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR105##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR106##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR107##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR108##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR109##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR110##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR111##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub. 3                                                                         OCH.sub.3                                      ##STR112##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR113##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     __________________________________________________________________________

    __________________________________________________________________________     ##STR114##                                                                   NZ,Z           R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                       __________________________________________________________________________     ##STR115##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR116##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR117##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR118##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR119##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR120##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR121##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR122##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR123##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR124##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR125##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR126##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR127##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR128##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR129##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR130##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                      ##STR131##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR132##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     __________________________________________________________________________

    __________________________________________________________________________     ##STR133##                                                                   NZ,Z           R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                       __________________________________________________________________________     ##STR134##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR135##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR136##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR137##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR138##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR139##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR140##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR141##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR142##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR143##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR144##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR145##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR146##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR147##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR148##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR149##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR150##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR151##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     __________________________________________________________________________

    __________________________________________________________________________     ##STR152##                                                                   NZ,Z           R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                       __________________________________________________________________________     ##STR153##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR154##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR155##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR156##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR157##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR158##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR159##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR160##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR161##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR162##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR163##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR164##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR165##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR166##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR167##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR168##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub. 3                                                                         OCH.sub.3                                      ##STR169##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                      ##STR170##    OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     __________________________________________________________________________

    __________________________________________________________________________     ##STR171##                                                                   NZ,Z            R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                      __________________________________________________________________________     ##STR172##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR173##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR174##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub. 3                                                                         OCH.sub.3                                     ##STR175##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR176##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR177##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR178##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR179##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR180##     OCH.sub.3                                                                          CH(CH.sub. 3).sub.2                                                                  OCH.sub.3                                                                          OCH.sub.3                                     ##STR181##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR182##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR183##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR184##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR185##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR186##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR187##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR188##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR189##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    cis + trans                                                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR190##                                                                   NZ,Z            R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                      __________________________________________________________________________     ##STR191##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR192##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR193##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                     ##STR194##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR195##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR196##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR197##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR198##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR199##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                          OCH.sub.3                                     ##STR200##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR201##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR202##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR203##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR204##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR205##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR206##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR207##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR208##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    cis + trans                                                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR209##                                                                   NZ,Z            R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                      __________________________________________________________________________     ##STR210##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR211##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR212##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR213##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR214##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR215##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR216##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR217##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR218##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR219##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR220##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR221##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR222##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR223##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR224##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR225##     OCH.sub. 3                                                                         CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR226##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR227##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    cis + trans                                                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR228##                                                                   NZ,Z            R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                      __________________________________________________________________________     ##STR229##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR230##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR231##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                    ##STR232##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR233##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR234##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR235##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR236##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR237##     OCH.sub.3                                                                          CH(CH.sub.3).sub. 2                                                                  OCH.sub.3                                                                          OCH.sub.3                                     ##STR238##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR239##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR240##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR241##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR242##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR243##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR244##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR245##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                     ##STR246##     OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    cis + trans                                                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR247##                                                                   NZ,Z            R.sub.2                                                                             R.sub.3                                                                              R.sub.4                                                                             R.sub.5                                    __________________________________________________________________________     ##STR248##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR249##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR250##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR251##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR252##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR253##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR254##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR255##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR256##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR257##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR258##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR259##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR260##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR261##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR262##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR263##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                            OCH.sub.3                                  ##STR264##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR265##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                  __________________________________________________________________________

    __________________________________________________________________________     ##STR266##                                                                   NZ,Z            R.sub.2                                                                             R.sub.6                                                                              R.sub.4                                                                             R.sub.5                                    __________________________________________________________________________     ##STR267##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR268##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR269##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR270##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR271##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR272##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR273##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR274##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR275##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR276##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR277##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR278##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR279##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR280##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR281##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR282##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR283##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR284##     OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                  __________________________________________________________________________

    ______________________________________                                         ##STR285##                                                                   NZ,Z               R.sub.2   R.sub.6                                          ______________________________________                                         ##STR286##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR287##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR288##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR289##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR290##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR291##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR292##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR293##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR294##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR295##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR296##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR297##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR298##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR299##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR300##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR301##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR302##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR303##        OCH.sub.3 CH(CH.sub.3).sub.2                               ______________________________________                                    

    ______________________________________                                         ##STR304##                                                                   NZ,Z               R.sub.2   R.sub.6                                          ______________________________________                                         ##STR305##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR306##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR307##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR308##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR309##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR310##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR311##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR312##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR313##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR314##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR315##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR316##        OCH.sub.3 CH(CH.sub. 3).sub.2                               ##STR317##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR318##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR319##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR320##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR321##        OCH.sub.3 CH(CH.sub.3).sub.2                                ##STR322##        OCH.sub.3 CH(CH.sub.3).sub.2                               ______________________________________                                    

    ______________________________________                                         ##STR323##                                                                   NZ,Z                 R.sub.2  R.sub.6                                         ______________________________________                                         ##STR324##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR325##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR326##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR327##          OCH.sub.3                                                                              C.sub. 6 H.sub.13                                ##STR328##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR329##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR330##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR331##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR332##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR333##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR334##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR335##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR336##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR337##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR338##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR339##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR340##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                 ##STR341##          OCH.sub.3                                                                              C.sub.6 H.sub.13                                cis + trans                                                                   ______________________________________                                    

    ______________________________________                                         ##STR342##                                                                   Y                     R.sub.3  R.sub.6                                        ______________________________________                                         ##STR343##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR344##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               (CH.sub.2).sub.4ONO.sub.2                                                                           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR345##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub. 3                                                                             C.sub.6 H.sub.13                                ##STR346##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR347##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR348##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR349##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR350##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR351##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR352##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR353##           OCH.sub.3                                                                              C.sub.6 H.sub. 13                              ______________________________________                                    

    ______________________________________                                         ##STR354##                                                                   Y                     R.sub.3  R.sub.6                                        ______________________________________                                         ##STR355##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR356##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               (CH.sub.2).sub.4ONO.sub.2                                                                           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR357##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR358##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR359##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR360##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR361##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR362##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR363##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR364##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR365##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               ______________________________________                                    

    ______________________________________                                         ##STR366##                                                                   Y                     R.sub.3  R.sub.6                                        ______________________________________                                         ##STR367##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR368##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               (CH.sub.2).sub.4ONO.sub.2                                                                           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR369##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub. 3                                                                             C.sub.6 H.sub.13                                ##STR370##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR371##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR372##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR373##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR374##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR375##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR376##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR377##           OCH.sub.3                                                                              C.sub.6 H.sub. 13                              ______________________________________                                    

    ______________________________________                                         ##STR378##                                                                   Y                     R.sub.3  R.sub.6                                        ______________________________________                                         ##STR379##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR380##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               (CH.sub.2).sub.4ONO.sub.2                                                                           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR381##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                               CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                                  OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR382##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR383##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR384##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR385##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR386##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR387##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR388##           OCH.sub.3                                                                              C.sub.6 H.sub.13                                ##STR389##           OCH.sub.3                                                                              C.sub.6 H.sub.13                               ______________________________________                                    

    __________________________________________________________________________     ##STR390##                                                                   Y                 R.sub.2                                                                             R.sub.6                                                                              R.sub.4                                                                             R.sub.5                                  __________________________________________________________________________     ##STR391##       OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                 ##STR392##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR393##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                             OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR394##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR395##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR396##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR397##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR398##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR399##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR400##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                __________________________________________________________________________

    __________________________________________________________________________     ##STR401##                                                                   Y                 R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                    __________________________________________________________________________     ##STR402##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   ##STR403##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR404##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                             OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR405##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR406##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR407##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR408##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR409##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR410##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR411##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  __________________________________________________________________________

    __________________________________________________________________________     ##STR412##                                                                   Y                 R.sub.2                                                                             R.sub.6                                                                              R.sub.4                                                                             R.sub.5                                  __________________________________________________________________________     ##STR413##       OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                 ##STR414##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR415##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                             OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR416##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR417##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR418##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR419##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR420##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR421##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                 ##STR422##       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                           "      OCH.sub.3                                                                           OCH.sub.3                                __________________________________________________________________________

    __________________________________________________________________________     ##STR423##                                                                   Y                 R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                    __________________________________________________________________________     ##STR424##       OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                   ##STR425##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR426##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2OCH.sub.2CH.sub.2ONO.sub. 2                                                             OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR427##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR428##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR429##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR430##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR431##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR432##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   ##STR433##       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                  __________________________________________________________________________

    __________________________________________________________________________     ##STR434##                                                                   Y                R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR435##      OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR436##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   (CH.sub.2).sub.4ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR437##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                            OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                             OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR438##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR439##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR440##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR441##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR442##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR443##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR444##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   (CH.sub.2).sub.3ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR445##                                                                   Y                R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                            R.sub.5                                     __________________________________________________________________________     ##STR446##      OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                          OCH.sub.3                                    ##STR447##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   (CH.sub.2).sub.4ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR448##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                            OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                             OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR449##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR450##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR451##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR452##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR453##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR454##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                    ##STR455##      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   (CH.sub.2).sub.3ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                          OCH.sub.3                                   __________________________________________________________________________

    __________________________________________________________________________     ##STR456##                                                                   Y                R.sub.2                                                                             R.sub.6 R.sub.4                                                                             R.sub.5                                  __________________________________________________________________________     ##STR457##      OCH.sub.3                                                                           CH(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                           OCH.sub.3                                 ##STR458##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.4ONO.sub.2                                                                      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR459##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                            OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                             OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR460##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR461##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR462##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR463##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR464##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR465##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                 ##STR466##      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.3ONO.sub.2                                                                      OCH.sub.3                                                                           "       OCH.sub.3                                                                           OCH.sub.3                                __________________________________________________________________________

    __________________________________________________________________________     ##STR467##                                                                   Y                R.sub.2                                                                            R.sub.6                                                                              R.sub.4                                                                             R.sub.5                                    __________________________________________________________________________     ##STR468##      OCH.sub.3                                                                          CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           OCH.sub.3                                   ##STR469##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                  (CH.sub.2).sub.4ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR470##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2OCH.sub.2CH.sub.2 ONO.sub.2                                                            OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                  CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                             OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR471##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR472##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR473##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR474##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR475##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR476##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                   ##STR477##      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                  (CH.sub.2).sub.3ONO.sub.2                                                                      OCH.sub.3                                                                          "      OCH.sub.3                                                                           OCH.sub.3                                  __________________________________________________________________________

    __________________________________________________________________________     ##STR478##                                                                   Y                  R.sub.2                                                                             R.sub.3                                                                             R.sub.4                                                                             R.sub.5                                  __________________________________________________________________________     ##STR479##        OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 ##STR480##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.4ONO.sub.2                                                                        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR481##        OCH.sub.3                                                                           "     OCH.sub.3                                                                            OCH.sub.3                               CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                               OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                               OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR482##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR483##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR484##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR485##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR486##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR487##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR488##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.3ONO.sub.2                                                                        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                __________________________________________________________________________

    __________________________________________________________________________     ##STR489##                                                                   Y                  R.sub.2                                                                             R.sub.3                                                                             R.sub.4                                                                             R.sub.5                                  __________________________________________________________________________     ##STR490##        OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                                 ##STR491##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.4ONO.sub.2                                                                        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR492##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2 OCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                               OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR493##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR494##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR495##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR496##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR497##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                 ##STR498##        OCH.sub.3                                                                           "     OCH.sub.3                                                                            OCH.sub.3                                ##STR499##        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                (CH.sub.2).sub.3ONO.sub.2                                                                        OCH.sub.3                                                                           "     OCH.sub.3                                                                           OCH.sub.3                                __________________________________________________________________________

    __________________________________________________________________________     ##STR500##                                                                   Y                 R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                    __________________________________________________________________________     ##STR501##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR502##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR503##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                             OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR504##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR505##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR506##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR507##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR508##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR509##       OCH.sub. 3                                                                         OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR510##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  __________________________________________________________________________

    __________________________________________________________________________     ##STR511##                                                                   Y                 R.sub.2                                                                            R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                    __________________________________________________________________________     ##STR512##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR513##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.4ONO.sub.2                                                                       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR514##       OCH.sub.3                                                                          OCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                  CH.sub.2OCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  CH.sub.2SCH.sub.2CH.sub.2ONO.sub.2                                                              OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR515##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR516##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR517##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR518##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR519##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR520##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                   ##STR521##       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  (CH.sub.2).sub.3ONO.sub.2                                                                       OCH.sub.3                                                                          OCH.sub.3                                                                            OCH.sub.3                                                                          OCH.sub.3                                  __________________________________________________________________________

The following Examples are given for tthe purpose of illustrating thepresent invention:

EXAMPLE 1

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate dihydrate.

3 g.2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl}-phenoxyaceticacid are dissolved in a mixture of 60 ml. methylene chloride and 1.27ml. triethylamine. A solution of 1 ml. ethyl chloroformate in 30 ml.methylene chloride is added dropwise thereto, while stirring, at -15° C.When the addition is finished, stirring is continued for 45 minutes at-15° C. and then 1.6 g. nitrooxyethylammonium nitrate is added thereto.Subsequently, while stirring at -15° C., a solution of 2.75 ml.triethylamine in 25 ml. methylene chloride is added dropwise thereto.The reaction mixture is further stirred for 30 minutes at -15° C., thendiluted with 50 ml. methylene chloride and washed several times withwater. The methylene chloride phase is dried over anhydrous sodiumsulphate and evaporated.

For further purification, the residue is chromatographed on a silica gelcolumn (220 g. silica gel 60; elution agent: methylene chloride/4%methanol). The column fractions obtained are evaporated, the residue isdissolved in methanol and the solution is mixed with a methanolicsolution of 0.8 g. oxalic acid dihydrate. The solution is evaporated andthe residue is treated with diisopropyl ether. There are obtained 3.75g. (87% of theory) of the title compound in the form of crystals; m.p.124°-125° C. (decomp.).

The following are prepared in an analogous manner:

EXAMPLE 2

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate; m.p. 115°-116° C. (decomp.).

EXAMPLE 3

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamideoxalate; m.p. 136°-137° C. (decomp.).

EXAMPLE 4

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-methyl-3-nitrooxypropyl-2)-acetamide

EXAMPLE 5

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamide

EXAMPLE 6

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N,N-bis-(nitrooxyethyl)-acetamideoxalate dihydrate; m.p. 105°-107° C. (decomp.).

EXAMPLE 7

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N,N-bis-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 118°-120° C. (decomp.).

The2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyacetic acid required as starting material is prepared as follows:

Step 1: 3-Methoxy-4-benzyloxy-α-isopropylbenzyl cyanide

150 g. 3-Methoxy-4-benzyloxybenzyl cyanide, together with 470 ml. 50%aqueous sodium hydroxide solution, 76 ml. 2-bromopropane and 6 g.benzyltributylammonium bromide are stirred for 5 hours at 55° C. Thereaction mixture is then poured into 4 liters of water and extractedseveral times with methylene chloride. The combined methylene chloridephases are dried over anhydrous sodium sulphate, evaporated and theresidue distilled in a high vacuum.

There are obtained 155 g. (90% of theory)3-methoxy-4-benzyloxy-α-isopropylbenzyl cyanide; b.p. 184°-186°C./6.10⁻² mm; m.p. 68°-70° C.

Step 2:α-Isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-benzyloxyphenylacetonitrile

36.6 g. 3-Methoxy-4-benzyloxy-α-isopropylbenzyl cyanide are dissolved in150 ml. anhydrous dimethylformamide. 30.3 g.(N-methyl-N-homoveratryl)-amine-γ-chloropropane are added thereto andthe mixture is warmed to 50° C. In the course of 1 hour, 5.7 g. 55%sodium hydride are added thereto, while stirring. After completion ofthe addition, stirring is continued for a further 2 hours at 50° C. andthe reaction mixture is then poured into 4 liters of water. This is thenextracted several times with methylene chloride and the combinedmethylene chloride phases are dried over anhydrous sodium sulphate andevaporated to dryness. For purification, the residue is chromatographedon a silica gel column (1.2 kg. silica gel; elution agent: methylenechloride/2% methanol). After evaporation of the column fractions, thereare obtained 45 g. (70% of theory)α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-benzyloxyphenylacetonitrileas an oily product.

Step 3:α-Isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-hydroxyphenylacetonitrile

45 g.α-Isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-benzyloxyphenylacetonitrileare dissolved in 400 ml. methanol and, after the addition of 4 g. Pd/C(10%) catalyst, hydrogenated. After the take up of the calculated amountof hydrogen, the catalyst is filtered off and the filtrate evaporated.There are obtained 36 g. (97% of theory)α-isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-hydroxyphenylacetonitrilein the form of an oily product.

Step 4: Ethyl2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyacetate

34.5 g.α-Isopropyl-α-[(N-methyl-N-homoveratryl)-amino-γ-propyl]-3-methoxy-4-hydroxyphenylacetonitrileare dissolved in 200 ml. dimethylformamide and mixed, while stirring atambient temperature, with 3.5 g. sodium hydride (55%). Stirring iscontinued for 15 minutes and then a solution of 9.8 ml. ethylbromoacetate in 50 ml. dimethylformamide is added dropwise thereto. Thetemperature is hereby not to exceed 30° C. After completion of theaddition, stirring is continued for 1 hour, the reaction mixture ispoured into 4 liters of water and extracted several times with methylenechloride. The combined methylene chloride phases are dried overanhydrous sodium sulphate and then evaporated. For purification, theresidue is chromatographed on a silica gel column (1.2 kg. silica gel;elution agent: methylene chloride/3% methanol). After evaporation of thecolumn fractions, there are obtained 33.3 g. (81% of theory) ethyl2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyacetatein the form of an oily product.

Step 5:2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid

Ethyl2-methoxy-4-<1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]>-phenoxyacetateare dissolved in 150 ml. ethanol. 125 ml. 1N aqueous sodium hydroxidesolution are added dropwise thereto at ambient temperature, whilestirring. After completion of the addition, stirring is continued for 1hour at ambient temperature and the alcohol then evaporated off. 125 ml.1N hydrochloric acid are then added thereto, followed by extractingseveral times with methylene chloride. The combined methylene chloridephases are dried over anhydrous sodium sulphate and evaporated. Thereare obtained 29.5 g. (94% of theory)2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]aminobutyl]}-phenoxyaceticacid as an oily product.

EXAMPLE 8

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate hydrate

4.5 g.2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid are dissolved in a mixture of 80 ml. methylene chloride and 1.9 ml.triethylamine. A solution of 1.35 ml. ethyl chloroformate in 30 ml.methylene chloride is added dropwise thereto at -15° C., while stirring.After completion of the addition, stirring is continued at -15° C. for afurther 45 minutes and then 2.3 g. nitrooxyethylammonium nitrate areadded thereto. Subsequently, a solution of 3.8 ml. triethylamine in 25ml. methylene chloride is added dropwise thereto at -15° C., whilestirring and the reaction solution is diluted with 50 ml. methylenechloride and washed several times with water. The methylene chloridephase is dried over anhydrous sodium sulphate and evaporated. Forpurification, the residue is chromatographed on a silica gel column (250g. silica gel; elution agent: methylene chloride/3% methanol). Thecolumn fractions obtained are evaporated, the residue is dissolved inmethanol and the solution is mixed with a methanolic solution of 1.25 g.oxalic acid dihydrate. The solution is evaporated and the residuetreated with diisopropyl ether. There are obtained 4.9 g. (78% oftheory) of the title compound in the form of crystals; m.p. 127°-129° C.(decomp.).

The following are prepared in an analogous manner:

EXAMPLE 9

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 132°-134° C. (decomp.).

EXAMPLE 10

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamideoxalate dihydrate; m.p. 123°-125° C. (decomp.).

EXAMPLE 11

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-methyl-3-nitrooxypropyl-2)-acetamideoxalate hydrate; m.p. 125°-127° C. (decomp.).

EXAMPLE 12

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamideoxalate hydrate; m.p. 140°-142° C. (decomp.).

EXAMPLE 13

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N,N-bis-(nitrooxyethyl)-acetamideoxalate hydrate; m.p. 105°-107° C. (decomp.).

EXAMPLE 14

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N,N-bis-(2-nitroxypropyl)-acetamideoxalate hydrate; m.p. 118°-120° C. (decomp.). (reaction with2-nitrooxypropylammonium-nitrate).

The2-methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid required as starting material is prepared analogously to2-methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid except that, instead of 3-methoxy-4-benzyloxybenzyl cyanide,3-benzyloxy-4-methoxybenzyl cyanide is used as starting material.

EXAMPLE 15

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate hydrate.

3 g.2-Methoxy-4-{2-[N-methyl-N-(4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid are dissolved in a mixture of 60 ml. methylene chloride and 1.3 ml.triethylamine. A solution of 1 ml. ethyl chloroformate in 30 ml.methylene chloride is added dropwise thereto at -15° C., while stirring.After completion of the addition, stirring is continued for 45 minutesat -15° C., 1.6 g. nitrooxyethylammonium nitrate is added thereto and asolution of 2.9 ml. triethylamine in 30 ml. methylene chloride is thenadded dropwise thereto. Stirring is continued for 30 minutes at -15° C.and the reaction solution is diluted with 50 ml. methylene chloride andwashed several times with water. The methylene chloride phase is driedover anhydrous sodium sulphate and evaporated. For further purification,the residue is chromatographed on a silica gel column (220 g. silicagel; elution agent: methanol/4% methylene chloride). The columnfractions obtained are evaporated, the residue is dissolved in methanoland the solution is mixed with a methanolic solution of 850 mg. oxalicacid dihydrate. The solution is evaporated and the residue treated withdiisopropyl ether. There are obtained 3.7 g. (85% of theory) of thetitle compound in the form of crystals; m.p. 132° C. (decomp.).

The following are prepared analogously:

EXAMPLE 16

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 135°-136° C. (decomp.).

EXAMPLE 17

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamideoxalate hydrate; m.p. 132°-134° C. (decomp.).

EXAMPLE 18

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-methyl-3-nitrooxypropyl-2)-acetamideoxalate hydrate; m.p. 122°-124° C. (decomp.).

EXAMPLE 19

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamideoxalate; m.p. 90°-92° C. (decomp.).

EXAMPLE 20

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N,N-bis-(nitrooxyethyl)-acetamideoxalate hydrate; m.p. 110°-112° C. (decomp.).

EXAMPLE 21

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N,N-bis-(2-nitrooxypropyl)-acetamideoxalate dihydrate; m.p. 110°-112° C. (decomp.).

EXAMPLE 22

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate dihydrate; m.p. 128°-130° C. (decomp.).

EXAMPLE 23

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate dihydrate; m.p. 135°-136° C. (decomp.).

EXAMPLE 24

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamideoxalate dihydrate; m.p. 123°-124° C. (decomp.).

EXAMPLE 25

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamideoxalate; m.p. 147°-149° C.

The2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid required as starting material is prepared as follows:

Step 1:α-Isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

48.5 g. α-Isopropyl-3,4-dimethoxyphenylacetonitrile are dissolved in 200ml. dimethylformamide. 40.8 g.N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]-N-(γ-chloropropyl)-amineare added thereto and the solution is warmed to 50° C. In the course of1 hour, 8.15 g. sodium hydride (55%) are added thereto. After completionof the addition, stirring is continued for 3 hours at 50° C. and thereaction mixture is poured into 4 liters of water and extracted severaltimes with methylene chloride. The combined methylene chloride phasesare washed with water, dried over anhydrous sodium sulphate andevaporated. For purification, the residue is chromatographed on a silicagel column (1.8 kg. silica gel; elution agent: methylene chloride/3%methanol). After evaporation of the column fractions, there are obtained52.8 g. (86% of theory) ofα-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrilein the form of an oily product.

Step 2:α-Isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-hydroxyphenyl)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrile

47.9 g.α-Isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrileare dissolved in 400 ml. methanol and, after the addition of 2 g. Pd/C(10%) catalyst, hydrogenated. After the take up of the calculated amountof hydrogen, the catalyst is filtered off and the filrate evaporated.There are obtained 38 g. (95% of theory)α-isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-hydroxy)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyphenylacetonitrilein the form of an oily product.

Step 3: Ethyl2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyacetate

37.7 g.α-Isopropyl-α-{[N-methyl-N-[2-(3-methoxy-4-hydroxy)-ethyl]]-amino-γ-propyl}-3,4-dimethoxyacetonitrileare dissolved in 200 ml. anhydrous dimethylformamide and mixed, whilestirring, with 3.7 g. sodium hydride (55%). Stirring is continued for 15minutes and then a solution of 10.7 g. ethyl bromoacetate in 100 ml.dimethylformamide is added dropwise thereto. The temperature shouldhereby not exceed 30° C. After completion of the addition, stirring iscontinued for 1 hour and the reaction mixture is then poured into 4liters of water and extracted several times with methylene chloride. Thecombined methylene chloride phases are washed with water, dried overanhydrous sodium sulphate and evaporated. The residue is purified bychromatographing on a silica gel column. (1.2 kg. silica gel; elutionagent: methylene chloride/3% methanol). After evaporation of the columnfractions, there are obtained 36.6 g. (81% of theory) ethyl2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyacetatein the form of an oily product.

Step 4:2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid

36.5 g. Ethyl2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyacetateare dissolved in 150 ml. ethanol. 140 ml. 1N aqueous sodium hydroxidesolution are added thereto dropwise at ambient temperature, whilestirring. Stirring is continued for 1 hour, then 140 ml. 1N hydrochloricacid are added thereto and the alcohol is evaporated off. The aqueousphase is extracted with methylene chloride. The methylene chloride phaseis dried over anhydrous sodium sulphate and evaporated. There areobtained 33.7 g. (97% of theory)2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid in the form of an oily product.

The N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]N-(γ-chloropropyl)-amineused as starting material in Step 1 is prepared as follows:

148 g. 3-Methoxy-4-benzyloxybenzyl cyanide are dissolved in 2.5 litersof methanol and, after the addition of 350 ml. liquid ammonia and 16 g.Raney nickel, hydrogenated at 100° C. and 80 ats. pressure. Thehydrogenation is finished after 4 hours. The catalyst is filtered off,the filtrate is evaporated and the residue is purifiedchromatographically on a silica gel column (1.6 kg. silica gel; elutionagent: methylene chloride/5% isopropylamine). After evaporation of thecolumn fractions, there are obtained 126 g. (84% of theory)3-methoxy-4-benzyloxy-β-phenylethylamine. This is dissolved in 500 ml.toluene and, after the addition of 48.5 ml. benzaldehyde, heated under awater separator. After completion of the separation of water, thereaction mixture is allowed to cool to ambient temperature and 46 ml.dimethylformamide are added thereto. Subsequently, it is heated underreflux for 30 minutes and then cooled to ambient temperature, two layersthereby being formed. The upper toluene layer is separated off anddiscarded. The lower layer is mixed with 500 ml. 80% ethanol andsubsequently heated under reflux for 30 minutes. The alcohol is thendistilled off and the residue taken up in methylene chloride. Themethylene chloride phase is extracted with concentrated hydrochloricacid and then discarded.

The aqueous phase is rendered alkaline with a concentrated aqueoussolution of sodium hydroxide, while cooling, an oil thereby separatingout. This is taken up in methylene chloride and the methylene chloridephase is dried over anhydrous sodium sulphate and evaporated. There areobtained 106 g. (80% of theory)3-methoxy-4-benzyloxy-β-phenyl-N-methylethylamine in the form of an oilyproduct. This is dissolved in 500 ml. dimethylformamide and, after theaddition of 132 g. of potash and 52 ml. 1-bromo-3-chloropropane, stirredfor 5 hours at ambient temperature. The reaction mixture is diluted withmethylene chloride and the insoluble residue filtered off with suction.The filtrate is diluted with water and extracted several times withmethylene chloride. The methylene chloride phases are combined, driedover anhydrous sodium sulphate and evaporated. For purification, theresidue is chromatographed on a silica gel column (1.2 kg. silica gel;elution agent: methylene chloride/3% methanol). After evaporation of thecolumn fractions, there are obtained 48.5 g. (36% of theory)N-methyl-N-[2-(3-methoxy-4-benzyloxy)-ethyl]-N-(γ-chloropropyl)-amine inthe form of an oily product.

EXAMPLE 262-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate

4.5 g.2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid are dissolved in a mixture of 80 ml. methylene chloride and 1.9 ml.triethylamine. A solution of 1.4 ml. ethyl chloroformate in 30 ml.methylene chloride is added dropwise thereto at -15° C., while stirring.After completion of the addition, stirring is continued for 45 minutesat -15° C., 2.3 g. nitrooxyethylammonium nitrate are added thereto andthen a solution of 3.8 ml. triethylamine in 30 ml. anhydrous methylenechloride is added dropwise thereto. Stirring is continued for 30 minutesat -15° C. and the reaction solution is diluted with 50 ml. methylenechloride and washed several times with water. The methylene chloridephase is dried over anhydrous sodium sulphate and evaporated. Forfurther purification, the residue is chromatographed over a silica gelcolumn (220 g. silica gel; elution agent: methylene chloride/3%methanol). The column fractions are evaporated, the residue is dissolvedin methanol and the solution is mixed with a methanolic solution of 1.2g. oxalic acid dihydrate. The solution is evaporated and the residuetreated with diisopropyl ether. There are obtained 4.5 g. (74% oftheory) of the title compound in the form of crystals; m.p. 128°-130° C.(decomp.).

The following are prepared analogously:

EXAMPLE 27

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 133°-135° C. (decomp.).

EXAMPLE 28

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxybutyl-2)-acetamideoxalate dihydrate; m.p. 123°-125° C.

EXAMPLE 29

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-methyl-3-nitrooxypropyl-2)-acetamideoxalate hydrate; m.p. 128°-130° C. (decomp.).

EXAMPLE 30

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(1,3-bis-nitrooxycyclohexyl-2)-acetamideoxalate hydrate; m.p. 143°-145° C. (decomp.).

EXAMPLE 31

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N,N-bis-(nitrooxyethyl)-acetamideoxalate hydrate; m.p. 110°-112° C. (decomp.).

EXAMPLE 32

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N,N-bis-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 118°-120° C. (decomp.).

The2-methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyacetic acid required as starting material was prepared analogously to2-methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid.

The following are prepared analogously:

EXAMPLE 33

3-{2-[N-Methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate; m.p. 134°-136° C. (decomp.).

EXAMPLE 34

3-{2-[N-Methyl-N-[4-cyano-4-dodecyl-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)acetamideoxalate hydrate; m.p. 140°-142° C. (decomp.).

EXAMPLE 35

3-{2-[N-Methyl-N-[4-cyano-4-dodecyl-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxyethyl)-acetamideoxalate hydrate; m.p. 127°-129° C. (decomp.).

EXAMPLE 36

3-{1-Cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate; m.p. 134°-136° C.

EXAMPLE 37

3-{1-Cyano-1-hexyl-4-[N-methyl-N-[2-(3-methoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate; oily.

EXAMPLE 38

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamideoxalate dihydrate; m.p. 140° C. (decomp.).

EXAMPLE 39

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamideoxalate dihydrate; m.p. 140° C. (decomp.).

EXAMPLE 40

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-(2,2-dimethyl-3-nitrooxypropyl-1)-acetamideoxalate dihydrate; m.p. 140° C. (decomp.).

EXAMPLE 41

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamideoxalate dihydrate; m.p. 132°-135° C. (decomp.).

EXAMPLE 42

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide citrate hydrate; m.p. 142°-145°C. (decomp.).

EXAMPLE 43

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 146°-147° C.(decomp.).

EXAMPLE 44

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 144°-146°C. (decomp.).

EXAMPLE 45

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide citrate hydrate; m.p. 143°-144°C. (decomp.).

EXAMPLE 46

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 142°-145°C. (decomp.).

EXAMPLE 47

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide citrate hydrate; m.p. 144°-146°C. (decomp.).

EXAMPLE 48

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(3-nitrooxypropyl-1)-acetamidecitrate hydrate; m.p. 141°-142° C. (decomp.).

EXAMPLE 49

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 139°-142°C. (decomp.).

EXAMPLE 50

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide citrate hydrate; m.p. 143°-144°C. (decomp.).

EXAMPLE 51

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4,5-trimethoxyphenyl)-butyl]-aminoethyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 142°-144°C. (decomp.).

EXAMPLE 52

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(nitrooxymethyl)-piperidylamide citrate hydrate; m.p. 145°-147°C. (decomp.).

EXAMPLE 53

2-Methoxy-4-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxyaceticacid 4-(α-nitrooxyethyl)-piperidylamide citrate hydrate; m.p. 143°-145°C. (decomp.).

EXAMPLE 54

3-{2-[N-Methyl-N-[4-cyano-4-hexyl-4-(3-methoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(nitrooxyethyl)-acetamideoxalate hydrate; m.p. 134°-135° C. (decomp.).

EXAMPLE 55

3-{2-[N-Methyl-N-[4-cyano-4-hexyl-4-(3-methoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 136°-137° C. (decomp.).

EXAMPLE 56

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(S(+)-2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 134°-135° C. (decomp.).

EXAMPLE 57

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-(R(-)-2-nitrooxypropyl)-acetamideoxalate hydrate; m.p. 126°-128° C. (decomp.).

EXAMPLE 58

2-Methoxy-4-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-[methyl-(2-nitrooxycyclohexyl)]-citratehydrate; m.p. 144°-146° C. (decomp.).

EXAMPLE 59

2-Methoxy-5-{1-cyano-1-(methylethyl)-4-[N-methyl-N-[2-(3,4-dimethoxyphenyl)-ethyl]-aminobutyl]}-phenoxy-N-[methyl-(2-nitrooxycyclohexyl)]-acetamidecitrate hydrate; m.p. 142°-143° C. (decomp.).

EXAMPLE 60

2-Methoxy-5-{2-[N-methyl-N-[4-cyano-4-(methylethyl)-4-(3,4-dimethoxyphenyl)-butyl]-aminoethyl]}-phenoxy-N-[methyl](2-nitrooxycyclohexyl)]-acetamidecitrate hydrate; m.p. 80° C. (decomp.).

The phenoxyacetic acids required as starting materials are prepared in amanner analogous to that described in the preceding Examples.

It will be understood that the specification and examples areillustrative but not limitative of the present invention and that otherembodiments within the spirit and scope of the invention will suggestthemselves to those skilled in the art.

What is claimed is:
 1. A phenylacetonitrile derivative compound of theformula ##STR522## wherein R₁, R₂, R₃, R₄ and R₅, are the same ordifferent and are hydrogen, fluorine, chlorine, bromine, C₁ -C₆ alkyl,C₁ -C₆ alkoxy, nitro, amino, or acylamino with up to 6 carbon atoms, ortwo adjacent substituents can together form methylenedioxy orethylenedioxy,A is ##STR523## wherein R₆ is straight-chained, cyclic orbranched, saturated or unsaturated alkyl containing 2 to 12 carbonatoms; R₇ is hydrogen or straight-chained or branched, saturated alkylcontaining up to 6 carbon atoms; m is 2 or 3; n is 2 or 3; p is 1 or 2;and X is amino-substituted or unsubstituted straight-chained, cyclic orbranched alkyl containing 2 to 10 carbon atoms, or is ##STR524## whereinY and Z, which can be the same or different, are straight-chained orbranched alkyl groups containing up to 8 carbon atoms or aremonocycloalkyl or dicycloalkyl, alkyl-monocycloalkyl oralkyl-dicycloalkyl, or monocycloalkylalkyl or dicycloalkylalkyl groups,which groups are uninterrupted or interrupted by an oxygen or sulphuratom, and one of the groups Z can further be hydrogen or both Z groupsare joined to form a ring containing 4 to 6 carbon atoms which isoptionally interrupted by a further nitrogen or a further nitrogen whichis substituted by alkyl or alkanoyl, the --O--NO₂ groups beingsubstituents of Y as well as of Z; and the salts thereof withphysiologically acceptable acids.
 2. The compound of claim 1 wherein R₂,R₄ and R₅ are C₁ -C₆ alkoxy, R₃ is hydrogen.
 3. The compound of claim 2wherein R₂, R₄ and R₅ are methoxy.
 4. The compound of claim 2 wherein Xis ##STR525## wherein Y and Z, are substituted with --O--NO₂ or areunsubstituted, can be the same or different, and are straight-chained orbranched alkyl containing up to 8 carbon atoms or are monocycloalkyl,alkylmonocycloalkyl or monocycloalkylalkyl having 4 to 6 carbons and upto 2 nitrogens in the cyclic moiety, and up to 8 carbons in the alkylmoiety or one of the groups Z in general formula II is hydrogen or bothZ groups are joined to form a ring containing 4 to 6 carbon atoms and upto one alkyl or alkanoyl substituted or unsubstituted nitrogen.
 5. Thecompound of claim 1 having the formula ##STR526##
 6. The compound ofclaim 5 whereinR₁ is hydrogen R₂ is --OCH₃ R₄ is --OCH₃ R₅ is --OCH₃ R₆is --CH(CH₃)₂
 7. The compound of claim 5 whereinX is ##STR527## whereinboth Z groups are joined to form a ring containing 4 to 6 carbon atomsand up to one alkyl or alkanoyl substituted or unsubstituted nitrogen.8. The compound of claim 1 whereinX is ##STR528##
 9. The compound ofclaim 1 wherein R₁, R₂, R₃, R₄ and R₅, are the same or different and arehydrogen, C₁ -C₆ alkyl or C₁ -C₆ alkoxy.
 10. The compound of claim 1wherein R₁, R₂, R₃, R₄ and R₅ are the same or different and are nitro,amino or acylamino with up to 6 carbon atoms.
 11. The compound of claim1 wherein R₁ and R₂ are adjacent substituents and together formmethylenedioxy or ethylenedioxy.
 12. The compound of claim 1 wherein R₃and R₄ are adjacent and together form methylenedioxy or ethylenedioxy.13. The compound of claim 1 wherein A is ##STR529##
 14. The compound ofclaim 1 wherein A is ##STR530##
 15. The compound of claim 1 wherein X isalkyl containing 2 to 10 carbon atoms.
 16. The compound of claim 1wherein X is amino substituted alkyl containing 2 to 10 carbon atoms.17. The compound of claim 1 wherein X is ##STR531##
 18. The compound ofclaim 1 wherein both Z groups are joined to form a ring containing 4 to6 carbon atoms or a ring containing 4 to 6 carbon atoms and a furthernitrogen.
 19. The compound of claim 1 wherein Y and Z are alkyl groupscontaining up to 8 carbon atoms.
 20. The compound of claim 1 wherein Xis ##STR532##
 21. A pharmaceutical composition containing an effectiveamount of the compound of claim 1 to lower the blood preload pressure onthe heart, for the treatment of heart and circulatory diseases, inadmixture with pharmaceutically acceptable diluents or carriers.
 22. Amethod for treatment of heart and circulatory diseases by reducing bloodpreload pressure of the heart, comprising administering an effectiveamount of the compound of claim
 1. 23. The method of claim 22 wherein 50mg to 500 mg per day per 75 kg of body weight, are administered.